High-Yield Synthesis of the Novel E,E-2,5-Dimethoxy-1,4-bis[2-(4-ethylcarboxylatestyril)]benzene by the Heck Reaction

Abstract

The novel E,E-2,5-dimethoxy-1,4-bis[2-(4-ethylcarboxylatestyril)]benzene, 4, was obtained in good yield (92%), by the Heck cross-coupling reaction using Pd(dba)₂ and P(OPh)₃ like catalytic system. The high trans specificity of the product produced by the Heck reaction was confirmed by Fourier Transform–infrared and NMR. The methodology reported can be used as synthetic route for precursors to phenylenevinylene target systems with highly desired functional groups in their molecular structure, such as carboxylic, to build metal–organic frameworks and other applications within the supramolecular chemistry.

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GRAPHICAL ABSTRACT

Keywords:

• Heck reaction
• phenylenevinylene
• trans configuration

ACKNOWLEDGMENTS

The authors wish to thank Professor Burkhard Koening, University of Regensburg, Germany, for the HR-MS experiments. Funding was supplied through grants from Colciencias and DIB-Universidad Nacional de Colombia. Special thanks to Dr. Fernando Aguirre for useful discussions.